WO2003093283A1 - Materiaux electroluminescents - Google Patents

Materiaux electroluminescents Download PDF

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Publication number
WO2003093283A1
WO2003093283A1 PCT/CN2003/000221 CN0300221W WO03093283A1 WO 2003093283 A1 WO2003093283 A1 WO 2003093283A1 CN 0300221 W CN0300221 W CN 0300221W WO 03093283 A1 WO03093283 A1 WO 03093283A1
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Prior art keywords
groups
group
emissive
halogen
alkyl
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PCT/CN2003/000221
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English (en)
Inventor
Chiming Che
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The University Of Hong Kong
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Publication date
Application filed by The University Of Hong Kong filed Critical The University Of Hong Kong
Priority to JP2004501422A priority Critical patent/JP4981252B2/ja
Priority to KR1020047017529A priority patent/KR100991874B1/ko
Priority to AU2003218866A priority patent/AU2003218866A1/en
Priority to EP03714623.0A priority patent/EP1499624B1/fr
Publication of WO2003093283A1 publication Critical patent/WO2003093283A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to light-emitting materials, which can be deposited as a thin layer by vacuum deposition, and which can be used as effective dopants in organic light- emitting devices (OLEDs).
  • OLEDs organic light- emitting devices
  • LED light-emitting diode
  • OLEDs organic light-emitting devices
  • gallium arsenide-based LEDs in the market are commonly available with efficiencies in some spectral regions exceeding conventional filtered fluorescent lamps.
  • inorganic semi-conductor materials are not compatible for large-area assembled displays.
  • some phosphorescent materials have intrinsic disadvantages, such as saturation of emission sites due to excessively long lifetimes as well as triplet-triplet annihilation and concentration quenching arising from strong intermolecular interactions at high doping levels (Phys. Rev. B. 60, 14422, (1999)).
  • quadridentate azomethine-zinc complexes have been used as blue light emitters in organic light-emitting devices, which exhibit maximum luminance of approximately 1000 cd/m 2 only (Jpn. J. Appl. Phys., 32, L511 (1993); US Patent 5,432,014).
  • Azomethme-aluminum/gallium complexes have been employed in OLEDs as emissive materials.
  • the current density of the device containing azomethine-gallium complex is 1 mA/cm 2 at 10 V and the electroluminescence is greenish blue (US Patent 6,316,130).
  • the main objective of this invention is to prepare organic light-emitting devices (OLEDs) doped with new light-emitting materials.
  • OLEDs organic light-emitting devices
  • the devices exhibit low turn-on voltages and high luminance and efficiencies.
  • An object of the present invention is to provide thermally stable, moisture-resistant me al-chelated materials that can be deposited as a thin layer of known thickness by a vapor deposition process.
  • the present invention concerns the design of high luminous dopants, which can be used at low concentration levels in light-emitting devices.
  • M represents Group 10 metal (including platinum) and R ⁇ -R 14 are each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; substituted aryl, with substitutents selected from the group consisting of halogen, lower alkyl and recognized donor and acceptor groups.
  • Embodiments of the present invention includes, but is not limited to, OLEDs comprising heterostructures for producing electroluminescence which contain anode (ITO glass substance), hole transport layer (NPB ( ⁇ -naphthylphenylbiphenyl amine)), matrix emissive layer [host material (beryllium bis(2-(2'-hydroxyphenyl)pyridine) (Bepp 2 )) with different concentration of dopants as illustrated by formula I and II herein], charge transport layer (lithium fluoride) and cathode (aluminum metal).
  • OLEDs comprising heterostructures for producing electroluminescence which contain anode (ITO glass substance), hole transport layer (NPB ( ⁇ -naphthylphenylbiphenyl amine)), matrix emissive layer [host material (beryllium bis(2-(2'-hydroxyphenyl)pyridine) (Bepp 2 )) with different concentration of dopants as illustrated by formula I and II herein], charge transport
  • the present invention provides new materials for applications as emissive dopants in electroluminescent devices.
  • the invention includes the synthetic methods for these novel complexes plus their use as hght-emitting materials.
  • the devices of the present invention can be applied to field of display, hght-emitter, display board for sign lamp, or light source for liquid crystal display.
  • FIG. 6a Electroluminescent spectrum of Device A containing complex lb (doping level 0.3 wt%)
  • Figure 6b Current density-voltage-luminance curve of Device A containing complex lb (doping level 0.3 wt%)
  • Figure 7a Electroluminescent spectrum of Device B containing complex lb (doping level 1.0 wt%)
  • Figure 7b Current density-voltage-luminance curve of Device B containing complex lb (doping level 1.0 wt%)
  • Figure 8. Electroluminescent spectrum of Device C containing complex lb (doping level 2.0 wt%) Detailed Description of the Invention
  • the inventions are generally related to syntheses, spectral characterization, phosphorescence, Ught-emitting properties of the new light-emitting materials, and their applications in OLEDs.
  • the examples are set forth to aid in an understanding of the inventions but are not intended to, and should not be interpreted to, limit in any way the invention as set forth in the claims which follow thereafter.
  • the photoluminescence (PL) of the platinum complexes lb and 2b in solution and as thin film are summarized in Table 2.
  • Table 2 The photoluminescence (PL) of the platinum complexes lb and 2b in solution and as thin film are summarized in Table 2.
  • the 298 K structureless emission of complex lb are observed at 595 and 599 nm in CH 2 C1 2 and as thin film respectively.
  • the PL properties of complex 2b in solution and as thin film are shown in Figure 3.
  • the emission maximum of 2b in thin film is shifted by 1704 cm "1 compared to that in solution.
  • complexes lb and 2b exhibit lifetimes of 1.9 and 5.3 ⁇ s in CH 2 C1 2 and luminescent quantum yields of 0.1 and 0.6 (with Ru(bpy) 3 Cl 2 as reference standard) respectively.
  • the device A was assembled as follows: indium tin oxide (ITO) electrode with sheet resistance of 20 ⁇ /square on glass substrate, a hole transport material NPB ( ⁇ - naphthylphenylbiphenyl amine) with thickness of 500 A, an emitting layer made of mixture of 0.3 wt.% complex lb and blue luminescent material Bepp 2 (beryllium bis(2-(2'- hydroxyphenyl)pyridine) with 400 A thickness, an enhanced charge transport layer LiF with thickness of 15 A, and aluminum layer with 2000 A thickness.
  • the metal and organic layers were laminated in sequence under 5 x 10 ⁇ 6 mbar without breaking vacuum between different vacuum deposition processes. The layers were deposited at rates of 2 or 5 A per second.
  • the emissive area of the device as defined by overlapping area of cathode and anode was 3 x 3 mm 2 .
  • the ITO coated glass slides were cleaned with organic solvents (acetone-isopropanol- methanol), deionized water, followed by ultra-violet-ozone cleaner.
  • EL spectra and current density-voltage-luminance characteristics of the devices were measured with a spectrophotometer and a computer-controlled direct-current power supply respectively at room temperature.
  • the device external efficiencies increase when the doping concentration levels of complex lb were adjusted from 2 to 0.3 wt%.
  • the specific examples are further illustrated as follows:
  • the performances of device A with 0.3 wt% doping level of complex lb are shown in Figures 6a and 6b.
  • Two intense EL emissions at 453 and 540 nm are observed when the device was driven under forward bias.
  • the current density-voltage-luminance characteristics curves of device A are also shown.
  • the turn-on voltage is approximately 6-7 V.
  • the maximum efficiency of the device was 4.1 cd/A at luminance of 2849 cd/m 2 .
  • the maximum luminance of 9325 cd/m 2 was obtained at driving voltage of 10 Y
  • the performances of device B with 1.0 wt% doping level of complex lb are shown in Figures 7a and 7b.
  • the device exhibits an intense EL emission peak at 546 nm and a weak emission at 457 nm.
  • the onset voltage of device B was approximately at 6-7 V.
  • the efficiency and maximum luminance were 1.9 cd/A at luminance of 1927 cd/m 2 and 6563 cd/m 2 at driving voltage of 9.5 V respectively.
  • doping level of greater than 5 % is reported to achieve dopant emission in organic or polymeric hght-emitting devices.
  • the OLEDs show virtually complete emission of complex lb when the doping level is around 2% and the efficiencies of devices increase from 1.5 to 4.1 cd/A when the doping levels of complex are decreased from 2.0 to 0.3 wt%.

Abstract

L'invention concerne des matériaux électroluminescents très lumineux, thermostables et résistant à l'humidité dérivés de ligands quadridentés de type ONNO et un métal du Groupe 10 utilisés comme dopants émissifs dans des dispositifs organiques électroluminescents. Les dopants sont des structures moléculaires représentées par les formules I et II dans lesquelles M représente un métal du Groupe 10 (notamment du platine), et R1-R14 sont chacun sélectionnés indépendamment dans le groupe constitué par hydrogène, halogène, alkyle, alkyle substitué, aryle, aryle substitué, des substituants étant sélectionnés dans le groupe constitué par halogène, alkyle inférieur et des groupes donneurs et accepteurs reconnus.
PCT/CN2003/000221 2002-05-01 2003-03-27 Materiaux electroluminescents WO2003093283A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2004501422A JP4981252B2 (ja) 2002-05-01 2003-03-27 電界発光材料
KR1020047017529A KR100991874B1 (ko) 2002-05-01 2003-03-27 전계 발광 물질
AU2003218866A AU2003218866A1 (en) 2002-05-01 2003-03-27 Electroluminescent materials
EP03714623.0A EP1499624B1 (fr) 2002-05-01 2003-03-27 Materiaux electroluminescents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/137,272 US6653654B1 (en) 2002-05-01 2002-05-01 Electroluminescent materials
US10/137,272 2002-05-01

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WO2003093283A1 true WO2003093283A1 (fr) 2003-11-13

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US (1) US6653654B1 (fr)
EP (1) EP1499624B1 (fr)
JP (2) JP4981252B2 (fr)
KR (1) KR100991874B1 (fr)
CN (1) CN100509827C (fr)
AU (1) AU2003218866A1 (fr)
TW (1) TWI267544B (fr)
WO (1) WO2003093283A1 (fr)

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WO2004096755A1 (fr) * 2003-04-30 2004-11-11 Takasago International Corporation Complexe de platine
WO2004108857A1 (fr) 2003-06-02 2004-12-16 Fuji Photo Film Co., Ltd. Dispositifs electroluminescents organiques et composes de complexes metalliques
WO2005056717A1 (fr) * 2003-12-05 2005-06-23 Eastman Kodak Company Element organique pour dispositifs electroluminescents
WO2006008069A1 (fr) 2004-07-16 2006-01-26 Merck Patent Gmbh Complexes metalliques
JP2006093197A (ja) * 2004-09-21 2006-04-06 Fuji Photo Film Co Ltd 有機電界発光素子
JP2006165526A (ja) * 2004-11-10 2006-06-22 Fuji Photo Film Co Ltd 有機電界発光素子
JP2006173588A (ja) * 2004-11-17 2006-06-29 Fuji Photo Film Co Ltd 有機電界発光素子
JP2006232784A (ja) * 2005-02-28 2006-09-07 Takasago Internatl Corp 白金錯体及び発光素子
US7332232B2 (en) 2004-02-03 2008-02-19 Universal Display Corporation OLEDs utilizing multidentate ligand systems
JPWO2005112520A1 (ja) * 2004-05-18 2008-03-27 日本放送協会 発光素子
DE102007017656A1 (de) * 2007-04-12 2008-10-16 Henkel Ag & Co. Kgaa Biheteroaryl-Metallkomplexe als Bleichkatalysatoren
US7732606B2 (en) 2004-09-27 2010-06-08 Fujifilm Corporation Light-emitting device
US7771845B2 (en) 2005-03-14 2010-08-10 Fujifilm Corporation Organic electroluminescent device
CN1772840B (zh) * 2005-04-27 2011-05-18 友达光电股份有限公司 金属络合物及包含其的磷光有机发光器件
US7947383B2 (en) 2004-09-22 2011-05-24 Fujifilm Corporation Organic electroluminescent device
US8153278B2 (en) 2008-04-24 2012-04-10 Fujifilm Corporation Organic electroluminescence device
US8187729B2 (en) 2007-09-14 2012-05-29 Fujifilm Corporation Organic electroluminescence device
US8216698B2 (en) 2008-04-22 2012-07-10 Fujifilm Corporation Organic electroluminescence device, novel platinum complex compound and novel compound capable of being a ligand thereof
US8257838B2 (en) 2003-05-09 2012-09-04 Fujifilm Corporation Organic electroluminescent device and platinum compound
CN109748936A (zh) * 2017-11-02 2019-05-14 广东阿格蕾雅光电材料有限公司 一种有机金属配合物发光材料

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JP4749744B2 (ja) * 2004-03-31 2011-08-17 富士フイルム株式会社 有機電界発光素子
US7361415B2 (en) * 2004-04-16 2008-04-22 The University Of Hong Kong System and method for producing light with organic light-emitting devices
US7247375B2 (en) * 2004-04-30 2007-07-24 Kimberly-Clark Worldwide, Inc. Polymeric matrices for the encapsulation of phosphorescent molecules for analytical applications
US20050244672A1 (en) * 2004-04-30 2005-11-03 Chi-Ming Che Organic light-emitting devices
US7238301B2 (en) * 2004-06-29 2007-07-03 Kimberly-Clark Worldwide, Inc. Cross-linked encapsulated phosphorescent molecules
JP4762527B2 (ja) 2004-11-10 2011-08-31 富士フイルム株式会社 有機電界発光素子
JP2006140218A (ja) * 2004-11-10 2006-06-01 Fuji Photo Film Co Ltd 有機電界発光素子
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JP4727262B2 (ja) * 2005-03-16 2011-07-20 富士フイルム株式会社 有機電界発光素子
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JP2007110067A (ja) * 2005-09-14 2007-04-26 Fujifilm Corp 有機電界発光素子用組成物、有機電界発光素子の製造方法、及び有機電界発光素子
US8956738B2 (en) 2005-10-26 2015-02-17 Global Oled Technology Llc Organic element for low voltage electroluminescent devices
EP1803789A1 (fr) 2005-12-28 2007-07-04 Novaled AG Utilisation de complexes métalliques comme émetteurs de luminiere a un dispositif lumineux organique et un tel dispositif
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DE102006030860A1 (de) * 2006-07-04 2008-01-10 Universität Regensburg Oligomere von Isonitril-Metallkomplexen als Triplett-Emitter für OLED-Anwendungen
DE102006035018B4 (de) 2006-07-28 2009-07-23 Novaled Ag Oxazol-Triplett-Emitter für OLED-Anwendungen
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US20090105488A1 (en) * 2007-10-22 2009-04-23 Chien-Hong Cheng Triptycene derivatives and their application
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DE102008048336A1 (de) 2008-09-22 2010-03-25 Merck Patent Gmbh Einkernige neutrale Kupfer(I)-Komplexe und deren Verwendung zur Herstellung von optoelektronischen Bauelementen
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KR101113139B1 (ko) * 2009-09-08 2012-02-15 이강옥 슬러지 탈수장치
EP2365556B1 (fr) 2010-03-08 2014-07-23 Semiconductor Energy Laboratory Co., Ltd. Élément électroluminescent, dispositif électroluminescent, dispositif électronique et dispositif d'éclairage
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JP5981736B2 (ja) * 2011-04-12 2016-08-31 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子、並びに、該有機電界発光素子を用いた発光装置、表示装置及び照明装置
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US9139699B2 (en) * 2012-10-04 2015-09-22 Dow Corning Corporation Metal containing condensation reaction catalysts, methods for preparing the catalysts, and compositions containing the catalysts
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US8772485B2 (en) * 2011-12-09 2014-07-08 The University Of Hong Kong Palladium complexes for organic light-emitting diodes
US10038153B2 (en) * 2014-04-03 2018-07-31 Versitech Limited Platinum (II) emitters for OLED applications
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5432014A (en) 1991-11-28 1995-07-11 Sanyo Electric Co., Ltd. Organic electroluminescent element and a method for producing the same
US6310360B1 (en) 1999-07-21 2001-10-30 The Trustees Of Princeton University Intersystem crossing agents for efficient utilization of excitons in organic light emitting devices
US6316130B1 (en) 1998-07-04 2001-11-13 Bayer Aktiengesellschaft Electroluminescent assemblies using azomethine-metal complexes

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2891783B2 (ja) * 1991-02-06 1999-05-17 パイオニア株式会社 有機エレクトロルミネッセンス素子
JP3615374B2 (ja) * 1997-11-17 2005-02-02 三洋電機株式会社 有機エレクトロルミネッセンス素子
GB9817845D0 (en) 1998-08-17 1998-10-14 Glaxo Group Ltd Chemical compounds
DE19846766A1 (de) * 1998-10-10 2000-04-20 Aventis Res & Tech Gmbh & Co Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften
JP2001003043A (ja) * 1999-06-16 2001-01-09 Mitsumi Electric Co Ltd 有機電界発光体及びそれを用いた電界発光素子
JP4154145B2 (ja) * 2000-12-01 2008-09-24 キヤノン株式会社 金属配位化合物、発光素子及び表示装置

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5432014A (en) 1991-11-28 1995-07-11 Sanyo Electric Co., Ltd. Organic electroluminescent element and a method for producing the same
US6316130B1 (en) 1998-07-04 2001-11-13 Bayer Aktiengesellschaft Electroluminescent assemblies using azomethine-metal complexes
US6310360B1 (en) 1999-07-21 2001-10-30 The Trustees Of Princeton University Intersystem crossing agents for efficient utilization of excitons in organic light emitting devices

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
APPL. PHYS. LETT., vol. 77, 2000, pages 904
CHEMICAL ABSTRACTS, 2000, Columbus, Ohio, US; abstract no. 134:50644, MAMULA OLIMPIA ET AL.: "Predetermined chirality at metal centers of various coordination geometries: a chiral cleft ligand for tetrahedral (T-4), square-planar(SP-4), trigonal-bipyramide(TB-5), square-pyramidal(SPY-5) and octahedral(OC-6) complexes" XP008065255 *
CHEMICAL ABSTRACTS, 2001, Columbus, Ohio, US; abstract no. 135:152935, TSUKADA N. ET AL.: "Synthesis and crystal structure of tristed dinuclear eta3-allylpalladium complexes containing tetradentate nitrogen ligands" XP008065241 *
NATURE, vol. 395, 1998, pages 151
P.CAPDEVIELLE ET AL.: "Electroactive polymers exchanging transition metal ions; synthesis of new monomers and polymers based on 6,6'-bis(2-hydroxyethyl)bipyridine complexes", NEW J. CHEM., vol. 18, 1994, pages 519 - 524
PHYS. REV B., vol. 60, 1999, pages 14422
See also references of EP1499624A4
SYNTHETIC METALS, vol. 93, 1998, pages 245

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EP1499624B1 (fr) 2016-01-06
US6653654B1 (en) 2003-11-25
US20030205707A1 (en) 2003-11-06
KR100991874B1 (ko) 2010-11-04
EP1499624A4 (fr) 2006-05-03
TW200427814A (en) 2004-12-16
KR20050007357A (ko) 2005-01-17
AU2003218866A1 (en) 2003-11-17
EP1499624A1 (fr) 2005-01-26
JP4981252B2 (ja) 2012-07-18
CN100509827C (zh) 2009-07-08
CN1649886A (zh) 2005-08-03

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